Study On The Synthesis Of Dibenzo-heptacyclic Compounds Containing Nitrogen

Dibenzo-heptacyclic compounds containing nitrogen is a kind of important drug intermediates,which show anticancer,anti-inflammatory,antidepressant and antibacterial biological activities.They are found in many familiar drugs,such as clozapine,dibenzepin and gastrozepin.It is a meaningful and challenging task for synthesis of dibenzo-heptacyclic compounds with new method.Exploring new methods can provide pharmaceutical chemists with methodological options for the synthesis of new molecules.The central iodine atom of hypervalent iodine reagents can react with electron-rich reactants,and finally gain a carbon positive ion intermediate.Thus,a series of oxidation rearrangements can be initiated.A new method mediated by hypervalent iodinereagents via Hofmann rearrangement and recyclization for the synthesis of dibenzo-heptacyclic compounds containing nitrogen was developed.In this paper,2-（2-nitrophenyl）methyl amino phenol was used as the reaction substrate.First,the reaction temperature,reagent,alkali,solvent were selected.It is found that the optimal conditions are ice salt bath,iodide benzene,potassium hydroxide and methanol.Then,the dibenzo-heptacyclic compounds with different substituents were synthesized under the optimal reaction conditions,and the effects of substrates with different substituents on the reaction were investigated.The yield of the target product is higher than that of the electron-withdrawing group when the benzene ring without the amide group contains the electron group.The yield is higher when the electron-withdrawing group is contained in the benzene ring with an amide group than when the electron group is contained in the target product.The application of the methodology was also explored.Finally,the possible mechanism of oxidative rearrangement cyclization is put forward through the related experimental verification.Also,the structure of products and the key substrates were confirmed by ¹H NMR,¹³C NMR,IR,HRMS.In addition,the application of the methodology was explored.Finally,the possible mechanism of oxidative rearrangement cyclization is put forward through the related experimental verification.